On thing that may not be so obvious in terms of rental vehicles would be ones that don't leak oil. I've had friends rent from various discount (not name brand) car rental companies and some of the older vehicles leaked a surprising amount of fluids (maybe oil).

If you're staying somewhere nice, you don't want to responsible for cleaning up oil stains on somebody's driveway. Relatively quiet is another nice thing. You don't want a screeching timing belt every time you start the car, regardless of what neighborhood you're in.

Another thing you don't want is to be dealing with a car breaking down on your vacation.

One slight disadvantage of the super big vehicles is that they can be a bit difficult to park in Paia and other places. It's not a huge problem, like it could be in San Francisco, but it's something to consider.

And on the topic of pickup trucks, I used to have a E-150 van and I sold it for a Tundra Extra Cab. It's much nicer driving in a car without the gear rattling around. However, after changing to a truck, I noticed that I was much more reluctant to drive around with lots of gear in my truck, and ended up spending much more time sailing in my backyard. Having had gear ripped off from me when I lived in Boston, and having had my bicycle stolen in San Francisco, I'm also cautious about having gear stolen, so I just don't feel that comfortable leaving too much in the back of my truck. That said, I've never worried about having an extra surfboard in the back of my truck while surfing at Hookipa, but if I go to eat in Paia, I put the board in the cab. That would not be so easy with windsurfing gear! On the other hand, maybe windsurfing gear never gets stolen and my mainland theft phobia is irrational?

Another factor is rain on the north shore. Having tons of soaking wet windsurfing gear is probably not ideal.

Overall, I think a mini-van for a couple or a full size van for more than 2 is idea for a windsurfing multi-sport vacation. That way, no matter where you go, you've always got the right gear. You could go surf or SUP at Kanaha before 11am, take a lunch with you, and be ready to windsurf at noon before the crowd gets there.

Justingordon, good points! Obviously the cars must be dependable and with no leaks, this is good for the renter, the landlord and for me, I do not want anybody to damage the engine because of not enough oil or coolant in the car. Squeaky belts can be a wake-up call for the whole neighborhood if someone decides to take this 7am yoga class.
Thanks for the input on the pick-up trucks, the gear is not as safe as in a closed vehicle and it may get wet if it rains.

I wouldn't leave a used Kleenex in a vehicle there, locked or unlocked. I never even carried a wallet when driving to the shore to sail. When I rent a car there, I add a cheap alarm.

Ummm...Pit Bulls is much more the norm out here.

Isobars, have you had any thefts? Most of the the thefts I've heard of come from leaving things like purses on car seats when going hiking in a remote spot. Otherwise, Maui is probably as safe as it gets. Still, you need some common sense. For example, right now there's a miss woman that went camping alone in a place well known to be home to many homeless.

Many houses in Maui still never lock any doors, and parking in Maui is still WAY safer than parking in San Francisco or any other big city.

Isobars, have you had any thefts? ... Maui is probably as safe as it gets.

Not personally, but friends have. I always left my rental car windows open to prevent broken windows, and I've never left anything in or on a car to be stolen since my buds saw the following operation there. A van rolls slowly down a residential street after dark until it nears a vehicle with WS boards on top. A passenger hops out and starts cutting tie-down straps. My buds headlight 'em and honk, and they split. The cops explain to my buds later that this a common scene. The thieves have piles of board boxes in the back of the van, pre-addressed and ready to throw on a plane to Asia or the U.S. mainland within the hour. Cops also told us not to leave gear on our upstairs balconies, because thieves scale the walls, throw your gear down, and it's gone.

I've also had buds awaken in the middle of the night to find intruders in the condo. (Sure wish somebody had tried that on my last trip, when we had about 10 guys sleeping all over the floor and furniture.)

The cops explain to my buds later that this a common scene. The thieves have piles of board boxes in the back of the van, pre-addressed and ready to throw on a plane to Asia or the U.S. mainland within the hour. Cops also told us not to leave gear on our upstairs balconies, because thieves scale the walls, throw your gear down, and it's gone.

This is news to me as well! It's best then to rent somewhere with plenty of gated off-street parking so you and your gear can sleep safely at night! I really do like the feeling of "home" when I hit my electric gate operator as I pull up to my place.

And on the topic of pickup trucks, I used to have a E-150 van and I sold it for a Tundra Extra Cab. It's much nicer driving in a car without the gear rattling around. However, after changing to a truck, I noticed that I was much more reluctant to drive around with lots of gear in my truck, and ended up spending much more time sailing in my backyard. Having had gear ripped off from me when I lived in Boston, and having had my bicycle stolen in San Francisco, I'm also cautious about having gear stolen, so I just don't feel that comfortable leaving too much in the back of my truck.

There are straps you can buy with inside a nylon strap and a lock. You can tie down your equipment in such a way that it cant be moved without cutting the metal straps. I use this in my truck. Ratchet down the board on top of everything else and it will deter the casual grab and run.

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